


Totally Professional

by missamericachavez



Category: Supernatural
Genre: Cheating, Drinking, F/M, Language, Smut
Language: English
Status: In-Progress
Published: 2018-12-06
Updated: 2018-12-06
Packaged: 2019-09-13 06:03:00
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,034
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16886994
Author URL: https://archiveofourown.org/users/missamericachavez/pseuds/missamericachavez
Summary: Reader has had a pretty tough week when she runs into her boss at a bar. Turns out he’s had a pretty shit week too.





	Totally Professional

You walk up to the bar, already fucked out of your mind, and plop down on the stool motioning to the bartender. When he walks over, you give him your dirtiest smile and use your arms and the bar top to push your boobs together and up to grab his interest.

“What can I get you honey?” he asks smiling wide, his eyes lingering on your tits. He’s cute enough you guess. Blonde hair ,blue eyes, and nice jawline. His nose is kind of crooked, but he’ll do. You’re not really looking for anything long term anyway.

“Can I get a whiskey?” you reply.

“No problem,” he winks as he walks off to make your drink. While you wait your eyes flitter over the bar. Your friends are off on the dance floor completely hammered making you laugh slightly. You’re not far off, but it’s not completely your fault. You’ve had a shitty week, you deserve this. You caught your boyfriend cheating on you a few days ago and you’ve been spiraling. When you found him, instead of begging for your forgiveness, he’d dumped you on the spot. He told you things had been bad anyway why force it? And honestly you agreed with him. Things had been truly awful between the two of you so he started banging his next door neighbor. But whatever you’re over it right? That’s why you’re downing shot after shot of everything liquor they’ve got on the shelf. It’s dumb, you shouldn’t be upset, but somehow you still were.

Things just kept getting better from there of course. Your car broke down, your mom called to tell you that your high school sweetheart was getting married, and your hot boss had been out for a few days for his grandma’s funeral leaving you with nothing to look forward to at work. He was honestly a huge factor into why you keep showing up everyday. Mr. Winchester has been the focus of almost all of your dirty fantasies since you’d started working as his secretary two years ago. The thought of his green eyes got you through so many masturbation sessions it’s not even funny. His stupid sexy smile was usually what you thought about when you were with your ex.

Mr. Winchester, “call me Dean”, is what he always says with that smirk and wink right after. He loves to flirt. That cocky bastard always knows just what to say and how to say it to make you weak in the knees. You would have left your lame ass boyfriend for Dean a long time ago if he wasn’t your boss and also married. You sigh as you look over the bar again. Maybe if you let the bartender fuck you from behind then you could pretend it’s Dean.

“Here ya go darlin’,” he says setting your drink down onto the bar top. You’re about to spin back around on your stool and thank him with your sexiest smile when something catches your eye. Tall man in a leather jacket and jeans with light hair like Dean’s and either you a truly tanked or your boss is at the other end of the bar looking like the sexiest biker to grace god’s green earth. You shoot the bartender a quick thanks grabbing your drink and hopping up from the bar in search of what you’re pretty sure you just saw. When you spot him, you know you’ve gotta be more drunk than you originally thought. The man you see everyday whom you thought practically lived in suits has on a plaid button down looking like a lumberjack. He’s standing with a guy taller than him, something you didn’t think possible, dressed much the same with hippie hair. Alright, someone drugged you that’s the only reason you can come up with for this amazing coincidence.

“Mr. Winchester?” you yell over the music as you get closer to him. His head jerks in your direction and you can automatically tell he’s just as tanked as you are. He smiles wider than you’ve ever seen excitedly yelling your name before pulling you into a giant hug. This is strange for you because the two of you of done a hell of a lot of flirting and you’ve teasingly grabbed his bicep, but that’s as far as the touching has ever gone. This bear hug is brand fucking new, but you can’t say you’re completely against it.

“Sammy! This is my secretary,” he yells to his friend using his beer to point at you as he tells the guy your name.

“The hot secretary?” Sammy tries to say for only Dean to hear, but he’s so drunk he can’t quite control the volume of his voice. Dean nods and Sammy looks you up and down nodding approvingly making you blush a little. “Nice to meet you it’s Sam not Sammy by the way.”

“Nice to meet you ‘Sam not Sammy’. Dean never told me he had a brother,” you say and he cringes.

“Wow thanks dude,” Sam says shoving Dean a little and Dean throws his hands up in the air.

“Don’t be offended. It’s mostly coffee and appointments with this one,” you say   
trying to help Dean out a little. “Such a professional.”

“You don’t have to lie,” Sam says scoffing. “He’s the least professional human to have existed ever.”

“Sorry,” you try, giggling as he tries for a bitch face, but ends up with a super goofy frown.

“Don’t worry about it,” he says laughing with you.

“I thought you were out of town at a funeral?” you ask turning to Dean who has his arm around your shoulder. You’ve gotta admit you like the feeling of him holding you like this even if it is only because he’s drunk.

“I lied I’ve had a tough week,” he says avoiding your eyes. “Needed to blow off some steam.” You can tell it’s more than just needing to blow off some steam from the heavy silence that falls over the three of you. You want to know more, but whatever it is can wait.

“Alright, well,” you say downing your whiskey in one gulp, “let’s blow off some steam then.” You grab his hand dragging him to the bar waving for Sam to follow too.

* * *

Several shots, a few songs full of bad dancing, and lot’s of “accidental” touches later you find yourself with your fingers laced with Deans walking to his sleek black muscle car. He drives you home and you’re not quite ready for the night to end just yet. He hops out of his car and walks you to your door.

“Thanks for bringing me home,” you say biting your lip trying to find the right words to say “please come inside and fuck me senseless” politely. That’s when you notice the wedding band on his left hand reminding you that life just isn’t fucking fair sometimes.

“No problem,” he says stepping way too close for a married man. “I had fun despite everything going on in my fucked up life. Thanks.”

“Well it’s late so… Goodnight,” you say ready to run into your apartment before you do something really fucking stupid like sleep with your very very married boss. You dig your keys out of your bag, ready to drown your sorrows in a pint of Ben & Jerry’s, when Dean’s fingers tangle in your hair tilting your lips up to meet his, muffling your squeal of surprise. You let him kiss you melting into his arms. You try rationalizing things in your head.  _Can’t be a homewrecker if I didn’t initiate it right_? You think as you pull him closer parting your lips for his tongue. When his lips leave yours, you’re breathless.

“Can I come inside?” he asks his voice raw as he whispers it hot against your ear.

“Yes,” you say immediately nodding and spinning around to shove your key in the door. You pause trying to get the top lock open when Dean presses tight against your ass rubbing his thick cock against you as he presses kisses along your jaw. You turn the lock, throw open the door, and pull Dean inside. Dean kicks the door shut behind him spinning you around, pushing you against the nearest wall, and covering your mouth with his. He presses his cock against you pressing the seam of your jeans into your clit. You moan against his lips as your hands grip his black under shirt pulling him impossibly closer.

“Bed?” he pants against your lips. You grab his hand and drag him down the hall to your bedroom. He pushes you lightly back onto the bed crawling over you, pulling off his shirts and moving onto his jeans as he watches you do the same. “Fuck,” he sighs as you slide your bra off of your arms. His fingers tease your nipples and you moan softly for him.

“Fuck me,” you gasp when he shoves his pants and underwear down his legs. His hard thick cock bobs in front of you as you remove the rest of your clothes. Dean lines his cock up at your entrance before pushing inside of you.

“You feel so good,” he groans rocking into you.

“Shit,” you cry out as his cock brushes against that spot inside of you. Dean thrusts hard into you and you moan, your back arching off of the bed. His balls slap against your ass as he fucks you pushing you higher and higher. His rhythm falters as he gets closer to the edge, his balls tightening when your pussy convulses around him.

“You ready to cum for me?” Dean asks speeding up his thrusts and circling your clit with his fingers. You nod your head, words escaping you at the moment. Your breath catches in your throat as you fall over the edge coming on his cock, Dean following not too far behind. The last thing you remember before you passed out, exhausted and drunk, is Dean being a huge fan of cuddles.

* * *

When you wake up the next morning, you have two strong arms wrapped around your waist scaring you momentarily before the events of last night come rushing back to you. It was honestly one of the best nights of your life, but this right here it can not last. He’s married and he’s your boss, what you’re doing isn’t ok. You sigh as you turn over to face him. He’s so peaceful you hate to ruin this for him, but you can’t let him stay here with you. You are not a homewrecker, you will not be that person. You will not risk your job for a man you barely know.

“You gonna watch me sleep all morning?” he asks poking one eye open.

“You gotta get up,” you say trying your hardest to put no emotion in your voice. Last night was great, but this has to end now. “You need to go home.”

“Oh ok,” he says looking a little hurt making you feel even worse.

“I’m sorry it’s just,” you sigh. “You’re married, and I know I was a little drunk last night but I don’t normally sleep with married men. My friend dated a married man once and I remember her telling me about how he couldn’t ever stay the night because he had to get home to his wife before she woke up in the morning. So I think at this point she’s probably worried sick right? So you gotta go.”

“Sweetheart,” he starts but you hold up a hand interrupting him.

“ We don’t have to talk about this. As far as I’m concerned it never happened, ok? You go back to your wife and your marital problems and I’ll go back to being your secretary.”

“Wait I,” he tries again.

“ No, I’m not a homewrecker. I’m not a bad person I don’t do this,” you interrupt again. “I can’t fuck up someone’s life like that it’s not fair to her and it’s not fair to me so just please-”

“I’m getting a divorce,” he says so quietly you barely hear him.

“Excuse me? What?” you had to have heard him wrong.

“I’m getting a divorce.”


End file.
